Purpose of Review - This paper discusses three scientific frontiers that need to be advanced in order to support decision-makers and practitioners in charge of operational decisions and action on the design and implementation of concrete adaptation policies and actions. These frontiers refer to going beyond the (1) incremental vs. transformational and (2) maladaptation vs. adaptation dichotomies and to advancing knowledge on (3) adaptation measures’ effectiveness and roles in designing context-specific adaptation pathways. Recent Findings - Dealing with adaptation to climate change on the ground often means answering three obvious but critical questions: what to do, where and when? These questions challenge the scientific community’s capacity to link conceptual advances (e.g. on transformative adaptation) and ground-rooted needs across sectors and regions (on solutions, governance arrangements, etc.). Summary - We argue that the three abovementioned frontiers represent the most burning challenges to the Adaptation Science community to help addressing climate-related societal needs. We also demonstrate that they are intertwined as moving one frontier forward will facilitate moving the others forward.